1. Field of the Invention
The present invention relates to novel phenyl-substituted bicyclooctane-1,3-dione derivatives, to a plurality of processes for their preparation and to their use as herbicides and/or pesticides.
2. Description of Related Art
Moreover, the invention relates to novel selective herbicidal active compound combinations comprising, firstly, phenyl-substituted bicyclooctane-1,3-dione derivates and, secondly, at least one crop plant compatibility-improving compound, which combinations can be used with particularly good results for the selective control of weeds and various crops of useful plants.
The present invention furthermore relates to increasing the activity of crop protection compositions comprising in particular phenyl-substituted bicyclooctane-1,3-dione derivates by adding ammonium salts or phosphonium salts and, if appropriate, penetrants, to the corresponding compositions, to processes for their preparation and to their use in crop protection as insecticides and/or for preventing unwanted plant growth.
It is known that certain substituted 2-arylcyclopentanediones have herbicidal, insecticidal and acaricidal properties (cf., for example, U.S. Pat. Nos. 4,283,348; 4,338,122; 4,436,666; 4,526,723; 4,551,547; 4,632,698; WO 96/01 798; WO 96/03 366, WO 97/14 667 and also WO 98/39281, WO 99/43649, WO99/48869, WO 99/55673, WO 01/17972, WO 01/74770, WO 03/062244, WO 04/080962, WO04/111042, WO05/092897, WO06/029799, WO07/080,066, WO07/096,058, WO 09/019,005, WO 09/019,015, WO 10/000,773, WO 10/081,894, WO 10/089,210 and WO 10/040,460). Also known are compounds which are substituted in a similar way: 3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-en-1-one from the publication Micklefield et. al., Tetrahedron, (1992), 7519-26 and the natural product Involution (−)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-enone from the publication Edwards et al., J. Chem. Soc. S, (1967), 405-9. An insecticidal or acaricidal action is not described. Moreover, 2-(2,4,6-trimethylphenyl)-1,3-indanedione is known from the publication J. Economic Entomology, 66 (1973), 584 and the laid-open publication DE-A 2 361 084 (U.S. Pat. No. 4,091,006), with herbicidal and acaricidal actions being stated.
However, in particular at low application rates and concentrations, the activity and activity spectrum of these compounds is not always fully satisfactory. Furthermore, the compatibility of these compounds with plants is not always sufficient.